4-Bromo-2-(trifluoromethyl)phenyl isocyanate → N-[4-bromo-2-(trifluoromethyl)phenyl]-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

HRID 2405356Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[CH:15]1([C:18]([N:20]2[CH2:24][CH2:23][C@@H:22]([CH2:25][C:26]([NH:28][NH2:29])=[O:27])[CH2:21]2)=[O:19])[CH2:17][CH2:16]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:29][NH:28][C:26](=[O:27])[CH2:25][C@@H:22]2[CH2:23][CH2:24][N:20]([C:18]([CH:15]3[CH2:17][CH2:16]3)=[O:19])[CH2:21]2)=[O:10])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a round-bottom flask was added 4-bromo-1-isocyanato-2-(trifluoromethyl)benzene (0.4 mL, 2.55 mmol) and dichloromethane (10 mL) under nitrogen. The mixture was cooled to −78° C. and a solution of 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (520 mg, 2.461 mmol) in dichloromethane (15 mL) was then added to the cooled solution and immediately allowed to warm to room temperature. After 1 h, analysis by LCMS indicated desired product formation. The resulting precipitate was collected and dried under vacuum filtration to yield the title product as a white solid (130 mg, 88%). MS(ES)+ m/e 476.9, 478.9 M+H]+.

Workup

temperatureto warm to room temperature

Sources & evidence

ORD record: ord-e5d941aeb7de48f8ba6042d42a9bb2fa
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802864B2

Reaction notes

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